


How It All Happened

by Pppiiieee



Category: Supernatural
Genre: Canon Divergence, Canonical Character Death, Dean Winchester Has a Sexuality Crisis, High School, Homophobic John Winchester, Homophobic Language, Implied Sexual Activity, Implied/ referenced blow jobs, M/M, No explicit descriptions though, Oneshot
Language: English
Status: Completed
Published: 2017-10-30
Updated: 2017-10-30
Packaged: 2019-01-26 11:33:08
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, Major Character Death, Underage
Chapters: 1
Words: 1,539
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12556484
Author URL: https://archiveofourown.org/users/Pppiiieee/pseuds/Pppiiieee
Summary: Dean is in high school and has his first experience with a guy.Flash forward and Dean tells Cas how he feels.





	How It All Happened

**Author's Note:**

> A little note on why I wrote this: I felt there needed to be a good reason why Dean hadn’t told Cas how he feels so when I got with my friend I made up a story. And of course she needed me to write out my ideas, and here we are! 
> 
> Please critique and leave your thoughts.

~Omaha, Nebraska, May 1995~

Another new city; whoopee. While the brothers left the car and grabbed their bags dad checks them into the shitty motel. They unpack in a small and less than welcoming room.  
Once settled. John gives the customary rundown to Dean while Sam readies his toiletries in the bathroom. “Blah, blah, blah, take care of Sammy, blah, shoot first ask questions later, blah, blah, take care of him, boy.” He was saying the same thing that he always does and the same thing that Dean has trained to tune out.

“Yes sir,” Dean replies as he always does.

“I’ll be back in a week.” Dad says as he drops some cash on the night stand, shouts his goodbyes, and exits the motel room to leave off to his next hunt.

Dean lies on the bed while Sam starts to prepare his school bag full of books for the next school. While Sammy had the brains, he had the ability to seduce (nearly) whichever girl he pleased. And at school tomorrow he planned to find a girl to seduce.

~~~

Dean had not expected what had happened though. It hadn’t been a girl who caught his attention but instead a very attractive boy.

In English he sat next to dark haired, blue eyed boy whom Dean fantasized about being fucked into the mattress by. That led to an unfortunate boner that would not quit taunting him. Needless to say he wasn’t too focused on the lesson at hand.

This boy was the one he wanted; he had a lip piercing and wore a Led Zeppelin t shirt with loose jeans. Dean was interested and aroused.

While showering that night Dean’s mind had drifted to the self-loathing and daddy issues part of his brain.

He would deny his attraction to men but his mind would always fantasize about being with one. He hadn’t dared to do that yet, but he hoped this time could be his first with a guy. This fact Dean could never share with anyone, especially his father. John was vocal about his opinions on gays- though he would choose to call them ‘fags’ or ‘fairies’. Dean had learned the hard way not to flirt with the wrong person unless he wanted a black eye. Though he knew it was wrong, he couldn’t help his attractions.

~~~~

The next day at lunch Dean spotted the boy sitting alone while eating what was supposed to be pizza. Somewhat confidently, he made his way over carrying his own tray of wannabe pizza.

“This seat taken?” Dean asked and gestured to the chair across from the boy. He shook his head and Dean dropped his tray and sat down.

“I’m Elliot, and you are…?” He said in a husky voice and Dean caught the slightest view of a tongue piercing which interested Dean even more.

“Dean.”

Elliot spoke again, “So, new kid, what brings you to our shithole of a school?”

Dean shrugged, “My dad’s work travels too damn much.”

Before responding his blue eyes dropped down to Dean’s lips while Elliot darted his tongue out and licked his own.

Yes, Dean thought to himself as a smirk crept onto his face, this boy was definitely the one.

“We’ve got English together; wanna get together after school to do some homework?” Elliot inquired before taking a bite of the pizza. 

“Yeah, that sounds good.” Dean hoped the question had an alternate meaning behind it.

“Meet me after school and we can walk to my house. It’s not too far from here and my mom works all night at the hospital so we’ll have the house to ourselves.”

Dean was thankful that he told Sam he might be home a little later that night. Being overly prepared for a hook up was one thing he could do well. He now couldn’t wait for the end of the day to come; it was taunting him, how close he was to getting Elliot in bed and fulfilling some of his never before experienced fantasies.

~~~~

The end of the school day hadn’t come soon enough; Dean hadn’t been able to think on anything but his hope for what after school would bring.

Dean met Elliot outside the school doors and Elliot gave a smile. Yes, he thought, this is totally the guy.

“Hey, Dean, you ready?”

“Hell yeah, let’s go.” Fuck, shit, that was too enthusiastic, you dummy, Dean’s mind scolded.

The walk to Elliot’s house was silent and quick. His house was aged and small but clearly well loved. There were flowers beside the walkway leading to the blue painted porch and dark green door. Dean admired Elliot’s ass as he unlocked the door and they made their way in. Pictures adorned the bright yellow walls and the house felt warm and welcoming. Dean couldn’t help but be jealous about all this; it was everything Dean never had.

“Dean,” Elliot asked, “Do you want something to drink? Water, milk, soda, something stronger…”

Dean watched Elliot’s lips as he spoke. He really wanted to kiss those lips. A little liquid courage could help him get there. “Do you have beer?”

Elliot nodded and opened the fridge and pulled two bottles out. From there on Dean’s mind was fairly calm, they went to the living room and did some homework and all went pretty well. The two flirted with each other obviously and sat close enough that their arms brushed often. 

Elliot eventually turned and kissed Dean in the middle of his sentence. Dean gasped before melting into the kiss. His worries slowly vanished and confidence filled its place. You can do this, it can’t be that much different, his mind supplied.

Luckily they were already seated on the couch so as Elliot leaned into Dean, he fell back slowly and they were making out quite passionately. They pulled back for air and Dean was speechless, how could something so great be wrong?

“Have you ever done this before?” Elliot questioned. 

“Um,” he was slightly unsure of how to answer this. Did he mean kissing, or sex, or being with a guy, or something else entirely? “Not any of this with a guy.”

To this Elliot chuckled. “It’s not that hard,” he said before their mouths connected again.

This led to them giving the other a sloppy blow job before Dean had to go back to the motel.

~~~~

When Dean returned to the motel room his mind was racing.

He had finally done something he’d been so scared to, and the world hadn’t collapsed, no one died from it, and the universe didn’t smite him so he took it as a win. It felt like something he could see himself continuing on with.

~~~~

Over the next two days Elliot and Dean had continued to see each other and mess around.

And on this day Sam had to stay after school for a study group and Elliot’s mom was home so going to the motel after had seemed like the logical solution.

Dean would never let himself remember how terrible his decision had been.

It started off normal as usual but had ended horribly; they did some homework before moving onto their extra-curricular activities. However as they were making out on Dean’s bed, John had come back from his hunt a little early, and walked in on the two.

They backed away as fast as they could but sadly John had seen.

“What the fuck is going on in here?!” John shouted. Before either could answer he turned to Elliot, “You get the fuck outta here!”

Elliot had grabbed his things and run out as fast as he could, and Dean hadn’t blamed him, he’d seen his father’s wrath and knew nobody would want to be on the receiving end of it.

The door slammed shut and Dean was terrified. “Dad?” he asked slowly.

“Don’t you ‘dad’ me; no son of mine would do that. No son of mine is a fag. I thought I’d raised you right and that your mother would be proud. She would hate this. She would hate you.” John was right in Dean’s face shouting and holding him there and he couldn’t help but cry. “Where’s Sam?”

“At school for a study group,” he said between whimpers.

His Dad had let him go and turned, “Get your stuff, get Sam’s stuff, we’re leaving.” The door shut loudly behind John and Dean was left alone.

Dean had spoken too soon, he wouldn’t continue on with any of this. He said then that he would never be with any guy again, for it had collapsed his world then.

~~~~

~North Cove, Washington, May 2017~

Dean was on his knees staring at Cas’ lifeless body. How could he not have told Cas. You were such a coward, so scared of Dad- who’s fucking dead- that you couldn’t tell him, he thought.

He’d long supressed that memory, his feelings, how he felt about Cas. It had scared him so much he wouldn’t dare let himself near another man in a romantic way- Elliot has been his first and only.

It was too late now, Cas was dead. Cas would never know how Dean felt.

“Cas,” Dean said with a broken voice, “I’m sorry, I love you.”

**Author's Note:**

> Thanks for reading! Have a nice day.
> 
> Feedback would be lovely


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